Diastereoselective Radical Tandem Addition‐Cyclization Reactions of Aromatic Tertiary Amines by Semiconductor‐Sensitized Photochemical Electron Transfer | Zendy

Marinković Siniša | Zendy; Hoffmann Norbert | Zendy

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Diastereoselective Radical Tandem Addition‐Cyclization Reactions of Aromatic Tertiary Amines by Semiconductor‐Sensitized Photochemical Electron Transfer

Author(s) -

Marinković Siniša,

Hoffmann Norbert

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400102

Subject(s) - chemistry , tandem , photochemistry , electron transfer , deuterium , photocatalysis , photoinduced electron transfer , radical cyclization , radical , semiconductor , homogeneous , radical ion , organic chemistry , catalysis , materials science , physics , quantum mechanics , composite material , thermodynamics , ion

The diastereoselective radical tandem addition‐cyclization reaction of N , N ‐dimethylaniline ( 2 ) with menthyloxyfuranone 1 was initiated by photochemically induced electron transfer using inorganic semiconductors (TiO 2 , ZnS, SiC and SnO 2 ) as sensitizers. The rearomatization step, which also causes the partial reduction of 1 , was studied by isotopic labeling experiments using deuterated derivatives of 2 . The influence of the semiconductor surface on these processes has been characterized and compared with the results obtained under homogeneous conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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